774-64-1

Basic information

• Product Name: 2(5H)-Furanone, 3,4-dimethyl-5-pentylidene-, (5Z)-
• Synonyms: 2(5H)-Furanone, 3,4-dimethyl-5-pentylidene-, (5Z)-;3,4-DIMETHYL-5-PENTYLIDENE-2-FURANONE;4-HYDROXY-2,3-DIMETHYL-2,4-NONADIENOICACIDGAMMALACTONE;BOVOLIDE;3,4-Dimethyl-5-pentylidene-2(5H)-furanone;Bovolid
• CAS NO: 774-64-1
• Molecular Formula: C11H16 O2
• Molecular Weight: 180.27
• Mol File: 774-64-1.mol
• Article Data: 7

Chemical Properties

• Boiling Point: 253.08°C (rough estimate)
• Flash Point: 118.1°C
• Appearance: /
• Density: 0.9976 (rough estimate)
• Vapor Pressure: 0.00192mmHg at 25°C
• Refractive Index: 1.4708 (estimate)
• CAS DataBase Reference: 2(5H)-Furanone, 3,4-dimethyl-5-pentylidene-, (5Z)-(CAS DataBase Reference)
• NIST Chemistry Reference: 2(5H)-Furanone, 3,4-dimethyl-5-pentylidene-, (5Z)-(774-64-1)
• EPA Substance Registry System: 2(5H)-Furanone, 3,4-dimethyl-5-pentylidene-, (5Z)-(774-64-1)

Safety Data

• Hazardous Substances Data: 774-64-1(Hazardous Substances Data)

Usage

Description

2(5H)-Furanone, 3,4-dimethyl-5-pentylidene-, (5Z)is a naturally occurring organic compound that is reportedly present in various food items such as peppermint oil, beef, tea, soybean, and maté (green, roasted). It is characterized by its buttery flavor and is known for its chemical properties as 4-Hydroxy-2,3-dimethyl-2,4-nonadienoic acid gamma-lactone.

Uses

Used in Flavor Industry:
2(5H)-Furanone, 3,4-dimethyl-5-pentylidene-, (5Z)is used as a flavoring agent for its distinct buttery flavor, enhancing the taste and aroma of various food products.
Used in Fragrance Industry:
Due to its unique scent, 2(5H)-Furanone, 3,4-dimethyl-5-pentylidene-, (5Z)is also utilized in the fragrance industry to add depth and complexity to perfumes and other scented products.
Used in Research and Development:
2(5H)-Furanone, 3,4-dimethyl-5-pentylidene-, (5Z)is employed in the scientific research and development sector for studying its chemical properties and potential applications in various fields, including pharmaceuticals and materials science.
Used in Analytical Chemistry:
2(5H)-Furanone, 3,4-dimethyl-5-pentylidene-, (5Z)can be used as a reference compound in analytical chemistry for the identification and quantification of similar compounds in complex mixtures, such as those found in the food and beverage industry.

InChI:InChI=1/C11H16O2/c1-4-5-6-7-10-8(2)9(3)11(12)13-10/h7H,4-6H2,1-3H3/b10-7+

Upstream product

• 201230-82-2 carbon monoxide 
• 109-72-8 n-butyllithium 
• 1033556-22-7 (Z)-5-(bromomethylene)-3,4-dimethylfuran-2(5H)-one 
• 2809-67-8 oct-2-yne 
• 65960-05-6 1-hexynylzinc chloride 
• 503-17-3 dimethylacetylene 
• 594-27-4 tetramethylstannane 
• 208194-69-8 3-Bromo-4-methyl-5-pent-(Z)-ylidene-5H-furan-2-one 
• 1360895-25-5 (Z)-3-iodo-4-methyl-5-pentylidenefuran-2(5H)-one 
• 18815-74-2 zinc methyl bromide 
• 6728-26-3 (E)-2-Hexenal 
• 60941-07-3 2-bromomethyl-but-2-enoic acid methyl ester 
• 208194-65-4 (E)-2-Bromo-3-methyl-non-2-en-4-ynoic acid ethyl ester 

Relevant articles and documents

A Copper(I)-Catalyzed Addition/Annulation Sequence for the Two-Component Synthesis of γ-Ylidenebutenolides

A highly efficient Cu(I)-catalyzed addition/annulation sequence has been developed for the synthesis of (Z)-ylidenebutenolides employing readily available α-ketoacids and alkynes as substrates. The reactions employ a simple commercially available Cu(I)-catalyst, display good substrate scope, and deliver products with high stereoselectivity. The synthetic utility of the method is demonstrated by the straightforward derivatization of the ylidenebutenolides into a diverse range of heterocycles, and also by the preparation of the natural product bovolide, and analogs thereof.

Carboxylate-directed tandem functionalisations of α,β- dihaloalkenoic acids with 1-alkynes: A straightforward access to (Z)-configured, α,β-substituted γ-alkylidenebutenolides

An easy and mild copper(I)-catalysed lactonisation of readily available (E)-2,3-dihalopropenoic acid derivatives regio- and stereoselectively leads to rarely described (Z)-3-halo-5-ylidene-5H-furan-2-ones. These compounds are subsequently able to undergo classical Pd-catalysed cross-coupling reactions, providing 3-substituted and 3,4-disubstituted 5-ylidene-5H-furan-2-ones (see scheme).

A novel protocol for the stereoselective synthesis of variously substituted (Z)-5-ylidene-5H-furan-2-ones

The Pd(II)- or Ag(I)-catalyzed lactonization of easily available (E)-4- (1-alkynyl)-2-bromopropenoic acids provides (Z)-3-bromo-5-ylidene-5H-furan- 2-ones, 5. These compounds, which represent an unpreviously reported class of (Z)-alkylidenebutenolides, are able to undergo Pd-catalyzed cross-coupling reactions with arylzinc halides, tetraalkylstannanes or alkenylstannanes to provide the corresponding 3-substituted (Z)-5-ylidene-5H-furan-2-ones, 1. The new procedure for the preparation of compounds 1 has been employed in a new synthesis of the butter flavour component bovolide.